KR830000904A - 페닐 알킬 아미노에틸 살리실아마이드와 제법 및 이를 함유하는 약제학적 조성물 - Google Patents
페닐 알킬 아미노에틸 살리실아마이드와 제법 및 이를 함유하는 약제학적 조성물 Download PDFInfo
- Publication number
- KR830000904A KR830000904A KR1019790003218A KR790003218A KR830000904A KR 830000904 A KR830000904 A KR 830000904A KR 1019790003218 A KR1019790003218 A KR 1019790003218A KR 790003218 A KR790003218 A KR 790003218A KR 830000904 A KR830000904 A KR 830000904A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- phenylpropyl
- protected
- salicylamide
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 238000002360 preparation method Methods 0.000 title claims 19
- -1 Phenyl alkyl aminoethyl salicylamide Chemical compound 0.000 title claims 3
- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- 230000003287 optical effect Effects 0.000 claims 24
- 239000002253 acid Substances 0.000 claims 14
- 239000000203 mixture Substances 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 12
- 229960000581 salicylamide Drugs 0.000 claims 11
- 231100000252 nontoxic Toxicity 0.000 claims 9
- 230000003000 nontoxic effect Effects 0.000 claims 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 238000009833 condensation Methods 0.000 claims 5
- 230000005494 condensation Effects 0.000 claims 5
- 239000003960 organic solvent Substances 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000006239 protecting group Chemical group 0.000 claims 5
- 239000003638 chemical reducing agent Substances 0.000 claims 4
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 4
- 238000000926 separation method Methods 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 238000004587 chromatography analysis Methods 0.000 claims 3
- 239000012458 free base Substances 0.000 claims 3
- 230000007062 hydrolysis Effects 0.000 claims 3
- 238000006460 hydrolysis reaction Methods 0.000 claims 3
- SGUAFYQXFOLMHL-ACJLOTCBSA-N (R,R)-labetalol Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(C(O)=CC=1)C(N)=O)CC1=CC=CC=C1 SGUAFYQXFOLMHL-ACJLOTCBSA-N 0.000 claims 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 2
- SGUAFYQXFOLMHL-UHFFFAOYSA-N 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 SGUAFYQXFOLMHL-UHFFFAOYSA-N 0.000 claims 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 2
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 239000011230 binding agent Substances 0.000 claims 2
- 229960001632 labetalol Drugs 0.000 claims 2
- 229910052744 lithium Inorganic materials 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000002844 melting Methods 0.000 claims 2
- 230000008018 melting Effects 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 2
- MAZMRYDRLXVGKU-CQSZACIVSA-N (2-carbamoylphenyl) 2-[[(2R)-4-phenylbutan-2-yl]amino]acetate Chemical compound C([C@@H](C)NCC(=O)OC=1C(=CC=CC=1)C(N)=O)CC1=CC=CC=C1 MAZMRYDRLXVGKU-CQSZACIVSA-N 0.000 claims 1
- ZASBYHZJHQFLGN-OAHLLOKOSA-N (2r)-n-benzyl-4-phenylbutan-2-amine Chemical compound C([C@@H](C)NCC=1C=CC=CC=1)CC1=CC=CC=C1 ZASBYHZJHQFLGN-OAHLLOKOSA-N 0.000 claims 1
- BHKMAOIKHVZJCC-UHFFFAOYSA-N 2-carbamoyl-4-[2-(4-phenylbutan-2-ylazaniumyl)acetyl]phenolate Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(=O)CNC(C)CCC1=CC=CC=C1 BHKMAOIKHVZJCC-UHFFFAOYSA-N 0.000 claims 1
- BHKMAOIKHVZJCC-CYBMUJFWSA-N 2-carbamoyl-4-[2-[[(2r)-4-phenylbutan-2-yl]azaniumyl]acetyl]phenolate Chemical compound C([C@@H](C)NCC(=O)C=1C=C(C(O)=CC=1)C(N)=O)CC1=CC=CC=C1 BHKMAOIKHVZJCC-CYBMUJFWSA-N 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000012448 Lithium borohydride Substances 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical class OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 230000029087 digestion Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 150000003893 lactate salts Chemical class 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 150000004701 malic acid derivatives Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004344 phenylpropyl group Chemical group 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 125000005498 phthalate group Chemical class 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 150000003890 succinate salts Chemical class 0.000 claims 1
- 239000000829 suppository Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Ophthalmology & Optometry (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94451678A | 1978-09-20 | 1978-09-20 | |
| US944516 | 1978-09-20 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840001867A Division KR890001998B1 (ko) | 1978-09-20 | 1984-04-09 | 페닐알킬아미노에틸살리실아미드의 제조방법 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR830000904A true KR830000904A (ko) | 1983-04-28 |
Family
ID=25481553
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019790003218A Ceased KR830000904A (ko) | 1978-09-20 | 1979-09-18 | 페닐 알킬 아미노에틸 살리실아마이드와 제법 및 이를 함유하는 약제학적 조성물 |
| KR1019840001867A Expired KR890001998B1 (ko) | 1978-09-20 | 1984-04-09 | 페닐알킬아미노에틸살리실아미드의 제조방법 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840001867A Expired KR890001998B1 (ko) | 1978-09-20 | 1984-04-09 | 페닐알킬아미노에틸살리실아미드의 제조방법 |
Country Status (27)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4658060A (en) * | 1982-04-26 | 1987-04-14 | Schering Corporation | Preparation of (-)-5-(beta)-1-hydroxy-2-((beta)-1-methyl-3-phenylpropyl)aminoethyl) salicylamide |
| IT1194406B (it) * | 1983-09-27 | 1988-09-22 | Scharper S P A | Procedimento per la preparazione di 2-idrossi-5-01-idrossi-2-((4-fenil-2-butil)ammino) etil benzammide |
| HU190867B (en) * | 1984-01-20 | 1986-11-28 | Egyt Gyogyszervegyeszeti Gyar,Hu | Process for preparing 2-hydroxy-5-/1-hydroxy-2-/1-methyl-3-phenyl-propyl/-amino/ethyl/-benzamide and pharmaceutically acceptable salts thereof |
| US4788183A (en) * | 1987-11-30 | 1988-11-29 | Schering Corporation | Method for treatment of dyslipidemia in humans |
| US4879233A (en) * | 1989-02-10 | 1989-11-07 | Schering Corporation | Novel Aspergillus niveus microorganism used for the chiral reduction of carbonyl groups |
| US6001884A (en) * | 1991-08-23 | 1999-12-14 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| EP0657029A4 (en) * | 1991-08-23 | 1996-02-07 | Nps Pharma Inc | CALCIUM RECEPTORS INFLUENCING MOLECULES. |
| US6031003A (en) * | 1991-08-23 | 2000-02-29 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US5688938A (en) * | 1991-08-23 | 1997-11-18 | The Brigham & Women's Hospital, Inc. | Calcium receptor-active molecules |
| US5858684A (en) * | 1991-08-23 | 1999-01-12 | The Brigham And Women's Hospital, Inc. | Method of screening calcium receptor-active molecules |
| US6313146B1 (en) | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6011068A (en) * | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US5763569A (en) * | 1991-08-23 | 1998-06-09 | The Brigham And Women's Hospital, Inc | Calcium receptor-active molecules |
| US5962314A (en) * | 1993-02-23 | 1999-10-05 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| JP2882882B2 (ja) | 1994-10-21 | 1999-04-12 | エヌピーエス・ファーマシューティカルズ・インコーポレイテッド | カルシウム受容体活性化合物 |
| EP0907631B1 (en) * | 1996-05-01 | 2003-06-18 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor-active compounds |
| IT1313583B1 (it) * | 1999-07-30 | 2002-09-09 | Chiesi Farma Spa | Derivati 2-amminotetralinici per la terapia del glaucoma. |
| ES2333266T3 (es) * | 2007-02-22 | 2010-02-18 | Indena S.P.A. | Procedimiento para la preparacion de sal de acetato del ester metilico de (2r,3s)-3-fenilisoserina. |
| EP2603215A4 (en) | 2010-08-11 | 2015-08-05 | Philadelphia Health & Educatio | NEW D3 DOPAMINE RECEPTOR AGONISTS FOR THE TREATMENT OF DYSKINESIA AT MORBUS PARKINSON |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1266058A (enrdf_load_stackoverflow) * | 1969-07-08 | 1972-03-08 | ||
| US4012444A (en) * | 1969-07-08 | 1977-03-15 | Allen & Hanburys Limited | 5-[1-Hydroxy-2-(1-methyl-3-phenylpropyl)aminoethyl] salicylamide and physiologically acceptable acid addition salts thereof |
| GB1541932A (en) * | 1975-04-17 | 1979-03-14 | Scherico Ltd | Diastereoisomers of a phenylalkylaminoethanol derivative |
-
1979
- 1979-09-13 ZA ZA00794872A patent/ZA794872B/xx unknown
- 1979-09-17 NO NO792993A patent/NO149660C/no unknown
- 1979-09-17 NZ NZ191589A patent/NZ191589A/en unknown
- 1979-09-17 DE DE7979103473T patent/DE2961263D1/de not_active Expired
- 1979-09-17 EP EP79103473A patent/EP0009702B1/en not_active Expired
- 1979-09-17 DK DK387579A patent/DK387579A/da not_active Application Discontinuation
- 1979-09-17 AU AU50881/79A patent/AU528626B2/en not_active Ceased
- 1979-09-17 CY CY1175A patent/CY1175A/xx unknown
- 1979-09-17 FI FI792884A patent/FI792884A7/fi not_active Application Discontinuation
- 1979-09-17 AT AT79103473T patent/ATE351T1/de not_active IP Right Cessation
- 1979-09-17 PH PH23042A patent/PH16794A/en unknown
- 1979-09-18 YU YU02273/79A patent/YU227379A/xx unknown
- 1979-09-18 PT PT70191A patent/PT70191A/pt unknown
- 1979-09-18 CA CA000335885A patent/CA1151211A/en not_active Expired
- 1979-09-18 OA OA56898A patent/OA06339A/xx unknown
- 1979-09-18 IE IE1770/79A patent/IE49301B1/en unknown
- 1979-09-18 IL IL58258A patent/IL58258A/xx unknown
- 1979-09-18 JP JP11996879A patent/JPS5555147A/ja active Granted
- 1979-09-18 GR GR60059A patent/GR73179B/el unknown
- 1979-09-18 KR KR1019790003218A patent/KR830000904A/ko not_active Ceased
- 1979-09-19 PL PL1979218408A patent/PL129114B1/pl unknown
- 1979-09-19 HU HU79SCHE690A patent/HU185523B/hu unknown
- 1979-09-19 DD DD79215640A patent/DD150457A5/de unknown
-
1983
- 1983-01-04 SG SG2/83A patent/SG283G/en unknown
- 1983-04-21 HK HK133/83A patent/HK13383A/xx unknown
- 1983-04-25 KE KE3283A patent/KE3283A/xx unknown
- 1983-11-17 JP JP58217073A patent/JPS59108749A/ja active Pending
-
1984
- 1984-04-09 KR KR1019840001867A patent/KR890001998B1/ko not_active Expired
-
1985
- 1985-12-30 MY MY42/85A patent/MY8500042A/xx unknown
-
1989
- 1989-11-13 JP JP1292552A patent/JPH02167253A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR830000904A (ko) | 페닐 알킬 아미노에틸 살리실아마이드와 제법 및 이를 함유하는 약제학적 조성물 | |
| EP0052492B1 (en) | 3-aryloxy-3-phenylpropylamines | |
| US5177112A (en) | Substituted 2-aminotetralins | |
| WO2000018764A1 (en) | Benzimidazolinyl piperidines as cgrp ligands | |
| HU214321B (hu) | Eljárás tramadol-N-oxid-származék, enantiomerjei és ezeket hatóanyagként tartalmazó gyógyszerkészítmények előállítására | |
| US6828342B2 (en) | Nitric esters and nitrate salts of specific drugs | |
| EP0283151A2 (en) | Prostaglandins useful for lowering intraocular pressure | |
| KR840001553B1 (ko) | 시클로헥센 유도체의 제조방법 | |
| US4743618A (en) | Substituted 2-aminotetralins | |
| US3557127A (en) | Substituted cyclohexenes,derivatives thereof and processes for obtaining same | |
| US4053509A (en) | Substituted aryl and aralkyl amides | |
| US3944675A (en) | Substituted aryl and aralkyl amides in the treatment of parkinsonism | |
| EP0254989B1 (en) | Substituted 2-aminotetralins | |
| EP0168543B1 (en) | (aralkylamino-2-or-propoxy)heterocyclic compounds | |
| US4194044A (en) | Process for preparing 3-phenoxy morphinans | |
| US4619919A (en) | Treatment of hypertension | |
| US3426037A (en) | Alpha-4-dimethylamino and pyrrolidino-1,2 diphenyl-3-methyl-2-butyl cyclopropane carboxylates | |
| US3824313A (en) | Topical opthalmic composition and methods of use | |
| CA1209586A (en) | Naphthalenecarboxamides, their production and use | |
| EP0108822B1 (en) | Antiglaucoma compounds | |
| EP0176049A2 (en) | Aminoalkylnaphtalene derivatives having pharmacological activities | |
| US3175945A (en) | Antihypertensive quaternary ammonium salts of 1:2:3:4-tetrahydroisoquinoline | |
| GB2139225A (en) | Novel acylaminophenol derivatives | |
| US3560511A (en) | Topical anaesthetic piperidyl carbinol | |
| US4950783A (en) | Treatment of hypertension |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19790918 |
|
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19830120 Patent event code: PE09021S01D |
|
| PG1501 | Laying open of application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 19830608 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 19830120 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |
|
| PJ2001 | Appeal |
Appeal kind category: Appeal against decision to decline refusal Decision date: 19841029 Appeal identifier: 1983201000543 Request date: 19830712 |